This Willie Nelson trivia quiz has 49 free questions with answers and follows the whole story: the Abbott, Texas kid raised by his grandparents who wrote his first song at seven, the Nashville songwriter behind Crazy and Hello Walls, the outlaw who moved to Austin and turned in Red Headed Stranger to executives who thought it was a demo, and the icon who co-founded Farm Aid, joined The Highwaymen and paid off a $32 million tax bill with an album. You'll get questions on his battered Martin guitar Trigger, the film that produced On the Road Again, the pop-standards album that sat on the country chart for ten years, his duet partners, his biodiesel and cannabis businesses, and the Halls of Fame he belongs to. Difficulty runs from easy fan questions to ones that only serious Willie people will get. Every answer has been checked against a primary reference and each question carries its citation.
30 of 49 questions with answers and explanations. Play the quiz
Q 01In which small Texas town was Willie Nelson born in 1933?
Abbott
He was born on April 29, though a doctor wrote down April 30. His mother left soon after and he was raised by his grandparents alongside his sister Bobbie.
Q 02At what age did Willie Nelson write his first song?
Seven
His grandfather had bought him a guitar the year before and taught him a few chords. By nine he was playing in a local Bohemian polka band.
Q 03Which Willie Nelson composition became Patsy Cline's signature hit and the most-played jukebox song ever?
Crazy
He wrote it in under an hour and originally called it 'Stupid'. Cline recorded her vocal in a single take while still bruised from a car accident.
Q 04Which singer had a 1961 hit with the Willie Nelson song 'Hello Walls'?
Faron Young
In the same era Nelson wrote 'Night Life' for Ray Price and 'Pretty Paper' for Roy Orbison, all while playing bass in Price's touring band.
Q 05Which branch of the US military did Willie Nelson join after high school, before a medical discharge?
Air Force
He lasted eight months. He later attended Baylor University from 1954 to 1956 without finishing.
Q 06To which city did Willie Nelson move in 1972, where the hippie music scene rejuvenated his career?
Austin
He had spent the 1960s in Nashville as a songwriter and RCA artist. The move made him the figurehead of the outlaw country movement.
Q 07What was the title of Nelson's 1973 Atlantic Records album that won great reviews but sold poorly?
Shotgun Willie
It was his first release after leaving RCA and marked the start of the looser, funkier sound of his Austin years.
Q 08Roughly how much did it cost to record the 1975 concept album Red Headed Stranger?
$20,000
It was cut at Autumn Sound in Garland, Texas. A Columbia executive asked why he was turning in a demo; Nelson replied, 'Ain't no demo.'
Q 09What crime is the fugitive of Red Headed Stranger on the run for?
Killing his wife and her lover
Nelson played the title character himself in a 1986 film adaptation. The album is number 183 on Rolling Stone's 500 greatest albums list.
Q 10Which Fred Rose song from Red Headed Stranger gave Willie Nelson his first number one hit as a singer?
Blue Eyes Crying in the Rain
The album went platinum in March 1976 and double platinum a decade later, and it was added to the National Recording Registry in 2009.
Q 11Who produced Stardust, Willie Nelson's 1978 album of pop standards?
Booker T. Jones
Columbia thought it would end his career. Instead it spent 540 weeks, a full decade, on the country albums chart and went quintuple platinum.
Q 12For how many weeks did Stardust stay on Billboard's country albums chart?
540
That is ten years. 'Georgia on My Mind' from the album won him a Grammy in 1979 and 'Blue Skies' went to number one.
Q 13Willie Nelson wrote 'On the Road Again' for which 1980 film he starred in?
Honeysuckle Rose
He reportedly wrote it on a barf bag when the film's producer asked for a song about touring. It was nominated for an Oscar and won the Grammy for Best Country Song.
Q 21In which city was the first Farm Aid concert held on September 22, 1985?
Champaign, Illinois
Eighty thousand people filled Memorial Stadium and the show raised over $9 million. Dave Matthews later joined the board.
Q 22How much did the IRS claim Willie Nelson owed when it seized his assets in 1990?
$32 million
He settled the debt with the auction of his belongings and the profits from a 1992 double album, The IRS Tapes: Who'll Buy My Memories?
Q 23What was the subtitle of The IRS Tapes, the 1992 album Willie Nelson released to pay off his tax debt?
Who'll Buy My Memories?
Q 14On what did Willie Nelson famously scribble the lyrics to 'On the Road Again'?
A barf bag
It peaked at number 20 on the Hot 100, entered the Grammy Hall of Fame in 2011 and has since turned up in Forrest Gump and Shrek.
Q 15Willie Nelson's 1982 hit 'Always on My Mind' peaked at what position on the Billboard Hot 100?
5
Elvis Presley and Brenda Lee had recorded it earlier; the Pet Shop Boys would take it to number one in Britain five years later.
Q 16With which Spanish crooner did Willie Nelson record 'To All the Girls I've Loved Before'?
Julio Iglesias
The unlikely 1984 pairing was a worldwide hit and won the CMA's single of the year.
Q 17'Pancho & Lefty', Willie Nelson's 1982 duet album, paired him with which fellow country legend?
Merle Haggard
The title track, written by Townes Van Zandt, gave both men a number one country single in 1983.
Q 18Which of these was NOT a member of the country supergroup The Highwaymen alongside Willie Nelson?
Merle Haggard
The quartet formed in 1985 and their Jimmy Webb-penned debut single 'Highwayman' went to number one on the country chart.
Q 19Who wrote 'Highwayman', the number one single that gave Willie Nelson's supergroup its name?
Jimmy Webb
The group also covered Guy Clark's 'Desperados Waiting for a Train' and released three albums between 1985 and 1995.
Q 20With which two musicians did Willie Nelson found Farm Aid in 1985?
John Mellencamp and Neil Young
The idea came from a remark Bob Dylan made at Live Aid about American family farmers. Nelson still serves as the organisation's president.
Its profits went straight to the government, and together with the auction of his assets it cleared the debt.
Q 24What is the name of Willie Nelson's famously battered nylon-string guitar?
Trigger
He named it after Roy Rogers's horse. It is a Martin N-20 he bought unseen in 1969 for $750 after a drunk damaged his Baldwin at Floore's Country Store.
Q 25Which company built Willie Nelson's famous nylon-string guitar?
Martin
It is an N-20 classical model with a Brazilian rosewood body and Sitka spruce top, and decades of flatpicking have worn a hole through it above the bridge.
Q 26Which musician was the first to carve his signature into the top of Nelson's famous guitar?
Leon Russell
He suggested scratching names rather than writing them so they would last. More than 100 signatures now cover the soundboard.
Q 27What did Willie Nelson vow to do if the IRS ever auctioned off his beloved guitar?
Quit performing
His daughter retrieved the guitar and his lawyer hid it until the debt was settled in 1993. Luthier Mark Erlewine has given it an annual check-up since 1977.
Q 28In which state was Willie Nelson's Ridgetop ranch, which burned down in December 1970?
Tennessee
The fire helped push him out of the Nashville orbit and back to Texas within two years.
Q 29What product did Willie Nelson's company Bio-Willie, formed in 2005, market to truck stops?
Biodiesel fuel
A decade later he launched his own cannabis brand, Willie's Reserve, in states where marijuana had been legalised.
Q 30What is the name of the cannabis brand Nelson announced in 2015?
Willie's Reserve
He has been one of the most visible advocates for legalisation in American music for decades.